Catalytic transfer hydrogenation and anticancer activity of arene–ruthenium compounds incorporating bi-dentate precursors

Chang, Yu‐Hsu; Leu, Wohn Jenn; Datta, Amitabha; Hsiao, Hung Chang; Lin, Chia Her; Guh, Jih‐Hwa; Huang, Jui Hsien

doi:10.1039/c5dt01310k

Cited by 16 publications

(6 citation statements)

References 78 publications

(5 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The C=S bond lengths were calculated as 1.76818 ( 1 ) and 1.77217 ( 2 ) Å using DFT and 1.712 ( 1 ) and 1.701 ( 2 ) Å from the XRD experiment. Furthermore, the N − C (coordinated N and thiocarbonyl C) bond lengths were shorter than the median value of 1.40 Å for all thiourea type complexes with an N − C bond, as indicated by the Cambridge Structural Database (CSD) . These shorter bond lengths might be due to the coordination through amidic N. The bond angles between ruthenium metal center and the three legs of the piano stool (N, S and Cl) were found to be 67–88 ° experimentally and theoretically, which was indicating the distortion from the regular octahedron (90 ° ).…”

Section: Resultsmentioning

confidence: 99%

Unusual coordination mode of aroyl/acyl thiourea ligands and their π‐arene ruthenium (II) piano‐stool complexes: Synthesis, molecular geometry, theoretical studies and biological applications

Rohini

Konakanchi

Prashanth

et al. 2019

Applied Organom Chemis

View full text Add to dashboard Cite

Two mononuclear ruthenium complexes (1 and 2) with aroyl/acylthiourea as an ancillary ligand of type, [(η6‐p‐cymene)RuCl(L‐N,S)], where [L1 = 2,4‐dichloro‐N‐(o‐tolylcarbamothioyl)benzamide] and L2 = N‐(phenylcarbamothioyl)cyclohexanecarboxamide] were synthesized and well characterized. The single crystal X‐ray diffraction studies revealed the coordination mode and the geometry of the complexes. The two complexes adopted general piano‐stool (three‐legged) geometry with a novel coordination mode of aroyl/acylthiourea through amide N (anionic) and thiocarbonyl S (neutral). This type of monobasic bidentate coordination of the aroyl/acylthiourea ligand was witnessed the first time around the metal ion. The coordination of the complexes was well explained through geometric parameters and frontier molecular orbital parameter values computed at the B3LYP/SDD level. The synthesized complexes were also screened for their antibacterial, antifungal, antioxidant and in vitro antiproliferative activities. Complexes exhibited good antimicrobial agents against various pathogens. The antioxidant activity of the complex 2 has shown most potent activity with IC50 value of 48.55 ± 1.7 μM compared to the reference drug. In addition, the in vitro antiproliferative activity of the complex 2 showed excellent activity against HepG‐2 cell line with the IC50 value of 24.30 ± 1.20 μM which is close to Doxorubicin standard drug.

show abstract

Section: Resultsmentioning

confidence: 99%

Unusual coordination mode of aroyl/acyl thiourea ligands and their π‐arene ruthenium (II) piano‐stool complexes: Synthesis, molecular geometry, theoretical studies and biological applications

Rohini

Konakanchi

Prashanth

et al. 2019

Applied Organom Chemis

View full text Add to dashboard Cite

show abstract

“…Although Meerwein–Ponndorf–Verley reduction has been widely utilized in both academic and industrial processes, the major drawbacks of this protocol are the requirement of a large amount of aluminum alkoxide reagent, unwanted side reactions, and moisture sensitivity of aluminum alkoxides. Over the last few decades, transfer hydrogenation of multiple bonds between carbon and heteroatoms (such as oxygen and nitrogen in carbonyls and imines, respectively) is a very active field of research and a large variety of homogeneous transition metal catalysts based on iron, − ruthenium, − osmium, − cobalt, − rhodium, − iridium, − nickel, − palladium, − and gold , have been developed. However, most of the efficient transfer hydrogenation protocols utilized ruthenium-, rhodium-, or iridium-based catalysts.…”

Section: Introductionmentioning

confidence: 99%

Transfer Hydrogenation of Aldehydes and Ketones in Air with Methanol and Ethanol by an Air-Stable Ruthenium–Triazole Complex

Ghosh

Jana

Panda

et al. 2021

ACS Sustainable Chem. Eng.

View full text Add to dashboard Cite

Coordination of 1,4-disubstituted 1,2,3-triazoles L 1 and L 2 with [(p-cymene)RuCl2]2 followed by dehydrochlorination in the presence of a base resulted in the formation of complexes 1 and 2, respectively. Both were tested for the transfer hydrogenation of aldehydes and ketones in air using ecologically benign and cheap ethanol as the hydrogen source in the presence of a catalytic amount of a base. Air-stable complex 1 was proved to be an active catalyst for the transfer hydrogenation of a wide variety of aromatic and aliphatic aldehydes and ketones bearing various functionalities. Catalyst 1 was also effective for the transfer hydrogenation of carbonyls using the simplest primary alcohol, methanol, under aerobic conditions. Under the present catalytic protocol, labile or reducible functionalities such as nitro, cyano, and ester groups were tolerated. Good selectivity was also observed for acyclic α,β-unsaturated carbonyls. However, this catalytic protocol was not selective for 2-cyclohexen-1-one as both alkene and keto moieties were reduced. The transfer hydrogenations are believed to proceed via a ruthenium-hydride intermediate. Finally, transfer hydrogenation of acetophenone using isopropanol as a commonly used hydrogen source was also performed and the sustainable and green credentials of these catalytic protocols utilizing methanol, ethanol, and isopropanol were compared with the help of the CHEM21 green metrics toolkit.

show abstract

“…[Ru(η 6 ‐ p ‐cymene)(κ 2 N,O ‐ l ‐glutammato)Cl] as well as [Ru(η 6 ‐arene)(κ 2 N,O ‐aa)Cl] complexes (arene = C 6 H 6 , C 6 Me 6 , p ‐cymene; aaH = l ‐proline, piperidine‐2‐carboxylate, N ‐methyl‐ l ‐phenylalanine) and the corresponding cationic trimers [Ru(η 6 ‐arene)(aa)] 3 [BF 4 ] 3 were found to be effective catalysts for the transfer hydrogenation of acetophenone and some related substrates, in 2‐propanol. [Ru(η 6 ‐cymene)(κ 2 N,O ‐ l ‐glutammato)Cl] was investigated also as potential anticancer drug; nevertheless it did not display any cytotoxicity against human prostate cancer cell lines (PC‐3 and DU‐145) . Other [Ru(η 6 ‐cymene)(κ 2 N,O ‐aa)Cl] complexes (aaH = glycine, l ‐proline, l ‐ or d ‐alanine, l‐ or d ‐phenylalanine) revealed to be inactive towards A2780 human ovarian cancer cells .…”

Section: Introductionmentioning

confidence: 99%

Ruthenium Arene Complexes with α‐Aminoacidato Ligands: New Insights into Transfer Hydrogenation Reactions and Cytotoxic Behaviour

et al. 2018

View full text Add to dashboard Cite

The Ru II arene complexes [Ru(η 6 -p-cymene)-(κ 2 N,O-aa)Cl] (aa = L-glutaminato, 1; L-homoserinato, 2; L-tyrosinato, 3; L-serinato, 4; L-prolinato, 5; trans-4-hydroxyl-L-prolinato, 6; L-threoninato, 7; glycinato, 8) were synthesized in high yields by the reactions of [Ru(η 6 -p-cymene)Cl 2 ] 2 with aa/MOH (M = Na, K). The salt [Ru(η 6 -p-cymene)(κ 2 N,O-L-serinato)(PPh 3 )]-[CF 3 SO 3 ], 9[CF 3 SO 3 ], was prepared in 68 % yield from 4 and AgSO 3 CF 3 /PPh 3 . All the products were fully characterized by analytical and spectroscopic methods, moreover the X-ray structures of 1 and 2 were elucidated by X-ray diffraction. Compounds 1-7 and 9[CF 3 SO 3 ] were studied as catalytic precursors for the transfer hydrogenation reaction (THR) of acetophenone, using 2-propanol or sodium formate (in water) as hydrogen [a]

show abstract

Catalytic transfer hydrogenation and anticancer activity of arene–ruthenium compounds incorporating bi-dentate precursors

Cited by 16 publications

References 78 publications

Unusual coordination mode of aroyl/acyl thiourea ligands and their π‐arene ruthenium (II) piano‐stool complexes: Synthesis, molecular geometry, theoretical studies and biological applications

Unusual coordination mode of aroyl/acyl thiourea ligands and their π‐arene ruthenium (II) piano‐stool complexes: Synthesis, molecular geometry, theoretical studies and biological applications

Transfer Hydrogenation of Aldehydes and Ketones in Air with Methanol and Ethanol by an Air-Stable Ruthenium–Triazole Complex

Ruthenium Arene Complexes with α‐Aminoacidato Ligands: New Insights into Transfer Hydrogenation Reactions and Cytotoxic Behaviour

Contact Info

Product

Resources

About